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Palladium-Catalyzed Ring-Opening Cyclization/Hydrosilylation of 1-Cyclopropyl-1,6-heptadienes to Form (E)-1-Butenyl Cyclopentanes

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    Palladium-Catalyzed Ring-Opening Cyclization/Hydrosilylation of 1-Cyclopropyl-1,6-heptadienes to Form (E)-1-Butenyl Cyclopentanes
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    Duke University, P. M. Gross Chemical Laboratory, Durham, North Carolina 27708-0346
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    Organometallics

    Cite this: Organometallics 2002, 21, 5, 901–905
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    https://doi.org/10.1021/om010907l
    Published February 7, 2002
    Copyright © 2002 American Chemical Society
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    Abstract

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    Reaction of 4,4-dicarbomethoxy-1-cyclopropyl-1,6-heptadiene (3) and HSiMe2OSiPh2t-Bu catalyzed by a 1:1 mixture of (phen)Pd(Me)Cl (2) (phen = 1,10-phenanthroline) and NaBAr4 [Ar = 3,5-C6H3(CF3)2] in CH2Cl2 at 0 °C for 12 h formed (E)-trans-3-(1-butenyl)-4-(3-tert-butyl-1,1-dimethyl-3,3-diphenyldisiloxymethyl)-1,1-dicarbomethoxycyclopentane (4) in 93% isolated yield as a 25:1 mixture of isomers. Reaction of 4,4-dicarbomethoxy-1-cyclobutyl-1,6-heptadiene (12a) and HSiMe2OSiPh2t-Bu (0.13 M) catalyzed by 2/NaBAr4 formed a 1.9:1 mixture of 1-pentenyl- (13a) and cyclobutylmethyl- (14a) cyclopentanes in 73% combined yield.

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    Experimental procedures and spectroscopic and analytical data for new dienes. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 22 publications.

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    13. Rebecca T. Ruck, Mark A. Huffman, Mary M. Kim, Michael Shevlin, Wynne V. Kandur, Ian W. Davies. Palladium‐Catalyzed Tandem Heck Reaction/CH Functionalization—Preparation of Spiro‐Indane‐Oxindoles. Angewandte Chemie 2008, 120 (25) , 4789-4792. https://doi.org/10.1002/ange.200800549
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    17. R.A. Widenhoefer, C.F. Bender. Silane-initiated Carbocyclization Catalyzed by Transition Metal Complexes. 2007, 367-410. https://doi.org/10.1016/B0-08-045047-4/00155-2
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    19. David W. Dodd, Heather E. Toews, Florentino d.S. Carneiro, Michael C. Jennings, Nathan D. Jones. Model intermolecular asymmetric Heck reactions catalyzed by chiral pyridyloxazoline palladium(II) complexes. Inorganica Chimica Acta 2006, 359 (9) , 2850-2858. https://doi.org/10.1016/j.ica.2005.11.025
    20. Björn C.G. Söderberg. Transition metals in organic synthesis: highlights for the year 2002. Coordination Chemistry Reviews 2004, 248 (11-12) , 1085-1158. https://doi.org/10.1016/j.ccr.2004.05.002
    21. M.K. Whittlesey. Metal Complexes as Catalysts for HX (XB, CN, Si, N, P) Addition to CC Multiple Bonds. 2003, 265-304. https://doi.org/10.1016/B0-08-043748-6/09127-1
    22. Xiang Wang, Sasha Z. Stankovich, Ross A. Widenhoefer. ChemInform Abstract: Palladium‐Catalyzed Ring ‐Opening Cyclization/Hydrosilylation of 1‐Cyclopropyl‐1,6‐heptadienes to Form (E)‐1‐Butenyl Cyclopentanes.. ChemInform 2002, 33 (31) https://doi.org/10.1002/chin.200231060
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    Organometallics

    Cite this: Organometallics 2002, 21, 5, 901–905
    Click to copy citationCitation copied!
    https://doi.org/10.1021/om010907l
    Published February 7, 2002
    Copyright © 2002 American Chemical Society
    Request reuse permissions

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